Thienylsulphonylamino(thio)carbonyl compounds

ABSTRACT

The invention relates to novel thienylsulphonylamino(thio)carbonyl compounds of the formula (I),  
                 
 
     in which  
     Q represents oxygen or sulphur,  
     R 1  represents cyano, halogen or in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms,  
     R 2  represents cyano, halogen or in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and  
     R 3  represents in each case optionally substituted heterocyclyl having 5 ring members, at least one of which represents oxygen, sulphur or nitrogen and one to three others may represent nitrogen,  
     and salts of compounds of the formula (I), to processes and novel intermediates for preparing the novel compounds and to their use as herbicides.

[0001] The invention relates to novelthienylsulphonylamino(thio)carbonyl compounds, to a plurality ofprocesses and novel intermediates for their preparation and to their useas herbicides.

[0002] It is already known that certain sulphonylaminocarbonyl compoundshave herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP431291, EP 507171, EP 534266, DE 4029753). However, the activity ofthese compounds is not in all respects satisfactory.

[0003] This invention, accordingly, provides the novelthienylsulphonylamino(thio)carbonyl compounds of the general formula(I),

[0004] in which

[0005] Q represents oxygen or sulphur,

[0006] R¹ represents cyano, halogen or in each case optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy,alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms,

[0007] R² represents cyano, halogen or in each case optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy,alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and

[0008] R³ represents in each case optionally substituted heterocyclylhaving 5 ring members, at least one of which represents oxygen, sulphuror nitrogen and one to three others may represent nitrogen,

[0009] and salts of compounds of the formula (I).

[0010] The novel thienylsulphonylamino(thio)carbonyl compounds of thegeneral formula (I) are obtained when

[0011] (a) sulphonamides of the general formula (II)

[0012]  in which

[0013] R¹ and R² are each as defined above,

[0014]  are reacted with (thio)carboxylic acid derivatives of thegeneral formula (III)

[0015]  in which

[0016] Q and R³ are each as defined above and

[0017] Z represents halogen, alkoxy, aryloxy or arylalkoxy,

[0018]  if appropriate in the presence of an acid acceptor and ifappropriate in the presence of a diluent,

[0019] or when

[0020] (b) sulphonyl iso(thio)cyanates of the general formula (IV)

[0021]  in which

[0022] Q, R¹ and R² are each as defined above,

[0023]  are reacted with heterocycles of the general formula (V)

H—R³⁻¹  (V)

[0024]  in which

[0025] R³⁻¹ represents optionally substituted heterocyclyl having 5 ringmembers, at least one of which represents >N—H,

[0026]  if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

[0027] or when

[0028] (c) sulphonyl chlorides of the general formula (VI)

[0029]  in which

[0030] R¹ and R² are each as defined above,

[0031]  are reacted with heterocycles of the general formula (V)

H—R³⁻¹  (V)

[0032]  in which

[0033] R³⁻¹ is as defined above under (b),

[0034]  and metal (thio)cyanates of the general formula (VII)

MQCN  (VII)

[0035]  in which

[0036] Q is as defined above and

[0037] M represents a metal equivalent,

[0038]  if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

[0039] or when

[0040] (d) sulphonyl chlorides of the general formula (VI)

[0041]  in which

[0042] R¹ and R² are each as defined above,

[0043]  are reacted with (thio)carboxamides of the general formula(VIII)

[0044]  in which

[0045] Q and R³ are each as defined above under formula (I),

[0046]  if appropriate in the presence of an acid acceptor and ifappropriate in the presence of a diluent,

[0047] or when

[0048] (e) sulphonylamino(thio)carbonyl compounds of the general formula(IX)

[0049]  in which

[0050] Q, R¹ and R² are each as defined above and

[0051] Z represents halogen, alkoxy, aryloxy or arylalkoxy,

[0052]  are reacted with heterocycles of the general formula (V)

H—R³⁻¹  (V)

[0053]  in which

[0054] R³⁻¹ is as defined above under (b),

[0055]  if appropriate in the presence of an acid acceptor and ifappropriate in the presence of a diluent,

[0056] and the compounds of the formula (I) obtained by the processes(a), (b), (c), (d) or (e) are, if appropriate, converted into salts bycustomary methods.

[0057] According to their nature, the processes (b), (c) and (e) areonly suitable for preparing those compounds of the formula (1) in whichR³ represents R³⁻¹.

[0058] The novel thienylsulphonylamino(thio)carbonyl compounds of thegeneral formula (I) have strong herbicidal activity.

[0059] The invention preferably provides compounds of the formula (I) inwhich

[0060] Q represents oxygen or sulphur,

[0061] R¹ represents cyano, halogen, represents optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in eachcase optionally cyano- or halogen-substituted C₂-C₄-alkenyl orC₂-C₄-alkinyl, represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each caseoptionally cyano- or halogen-substituted C₂-C₄-alkenyloxy orC₂-C₄-alkinyloxy,

[0062] R² represents cyano, halogen, represents optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in eachcase optionally cyano- or halogen-substituted C₂-C₄-alkenyl orC₂-C₄-alkinyl, represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each caseoptionally cyano- or halogen-substituted C₂-C₄-alkenyloxy orC₂-C₄-alkinyloxy, and

[0063] R³ represents in each case optionally substituted heterocyclyl ofthe formulae below

[0064]  in which

[0065] Q¹, Q² and Q³ each represent oxygen or sulphur and

[0066] R⁴ represents hydrogen, hydroxyl, amino, cyano, representsC₂-C₁₀-alkylideneamino, represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, represents in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₂-C₆-alkenylor C₂-C₆-alkinyl, represents in each case optionally fluorine-,chlorine-, bromine-, cyano-, C₁-C₄-alkoxy- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino orC₁-C₆-alkyl-carbonylamino, represents C₃-C₆-alkenyloxy, representsdi-(C₁-C₄-alkyl)-amino, represents in each case optionally fluorine-,chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkylamino or C₃-C₆-cycloalkyl-C₁-C₄-alkyl,or represents in each case optionally fluorine-, chlorine-, bromine-,cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl and/orC₁-C₄-alkoxy-substituted phenyl or phenyl-C₁-C₄-alkyl,

[0067] R⁵ represents hydrogen, hydroxyl, mercapto, amino, cyano,fluorine, chlorine, bromine, iodine, represents optionally fluorine-,chlorine-, bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, represents in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₂-C₆-alkenylor C₂-C₆-alkinyl, represents in each case optionally fluorine-,chlorine-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substitutedC₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino orC₁-C₆-alkyl-carbonylamino, represents C₃-C₆-alkenyloxy,C₃-C₆-alkinyloxy, C₃-C₆-alkenylthio, C₃-C₆-alkinylthio,C₃-C₆-alkenylamino or C₃-C₆-alkinylamino, representsdi-(C₁-C₄-alkyl)-amino, represents in each case optionally methyl-and/or ethyl-substituted aziridino, pyrrolidino, piperidino ormorpholino, represents in each case optionally fluorine-, chlorine-,bromine-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio,C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkylthio orC₃-C₆-cycloalkyl-C₁-C₄-alkylamino, or represents in each case optionallyfluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substitutedphenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio,phenyl-C₁-C₄-alkylthio, phenylamino or phenyl-C₁-C₄-alkylamino, or

[0068] R⁴ and R⁵ together represent optionally branched alkanediylhaving 3 to 11 carbon atoms, furthermore

[0069] R⁶, R⁷ and R⁸ are identical or different and each representhydrogen, cyano, fluorine, chlorine, bromine, or represent in each caseoptionally fluorine-, chlorine-, bromine- or C₁-C₄-alkoxy-substitutedalkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio,alkenylthio, alkinylthio, alkylsulphinyl or alkylsulphonyl having ineach case up to 6 carbon atoms or represent optionally cyano-,fluorine-, chlorine-, bromine or C₁-C₄-alkyl-substituted cycloalkylhaving 3 to 6 carbon atoms.

[0070] The invention furthermore preferably provides sodium, potassium,magnesium, calcium ammonium, C₁-C₄-alkyl-ammonium,di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium,tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- orC₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts ofcompounds of the formula (I) in which Q, R¹, R² and R³ each have themeaning given above as being preferred.

[0071] The invention in particular provides compounds of the formula (I)in which

[0072] Q represents oxygen or sulphur,

[0073] R¹ represents cyano, fluorine, chlorine, bromine, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,represents in each case optionally cyano-, fluorine- orchlorine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- ort-butoxy, or represents in each case optionally cyano-, fluorine- orchlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,

[0074] R² represents cyano, fluorine, chlorine, bromine, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,represents in each case optionally cyano-, fluorine- orchlorine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- ort-butoxy, or represents in each case optionally cyano-, fluorine- orchlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,and

[0075] R³ represents in each case optionally substituted heterocyclyl ofthe formulae below

[0076]  in which

[0077] Q¹, Q² and Q³ each represent oxygen or sulphur and

[0078] R⁴ represents hydrogen, hydroxyl, amino, represents in each caseoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in eachcase optionally fluorine-, chlorine- or bromine-substituted propenyl,butenyl, propinyl or butinyl, represents in each case optionallyfluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representspropenyloxy or butenyloxy, represents dimethylamino or diethylamino,represents in each case optionally fluorine-, chlorine-, methyl- and/orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally fluorine-,chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenylor benzyl

[0079] R⁵ represents hydrogen, hydroxyl, mercapto, amino, fluorine,chlorine, bromine, represents in each case optionally fluorine-,chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, represents in each case optionallyfluorine-, chlorine- or bromine-substituted ethenyl, propenyl, butenyl,propinyl or butinyl, represents in each case optionally fluorine-,chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, represents propenyloxy,butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio,butenylthio, propinylthio, butinylthio, propenylamino, butenylamino,propinylamino or butinylamino, represents dimethylamino, diethylamino ordipropylamino, represents in each case optionally fluorine-, chlorine-,methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, or represents in eachcase optionally fluorine-, chlorine-, methyl-, trifluoromethyl-,methoxy- and/or methoxycarbonyl-substituted phenyl, benzyl, phenoxy,benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or

[0080] R⁴ and R⁵ together represent optionally branched alkanediylhaving 3 to 11 carbon atoms, furthermore

[0081] R⁶, R⁷ and R⁸ are identical or different and each representhydrogen, cyano, fluorine, chlorine, bromine, or represent in each caseoptionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl,propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- ort-butoxy, propenyloxy, butenyloxy, propinyloxy, butinyloxy, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio,butenylthio, propinylthio, butinylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, or represent cyclopropyl.

[0082] A very particularly preferred group of compounds according to theinvention are those compounds of the formula (I) in which

[0083] Q represents oxygen or sulphur,

[0084] R¹ represents methyl, ethyl, n- or i-propyl,

[0085] R² represents methyl, ethyl, n- or i-propyl and

[0086] R³ represents optionally substituted triazolinyl of the formulabelow

[0087]  in which

[0088] Q¹ represents oxygen or sulphur and

[0089] R⁴ represents in each case optionally fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, representsin each case optionally fluorine- or chlorine-substituted propenyl orpropinyl, represents methoxy, ethoxy, n- or i-propoxy, methylamino,ethylamino, n- or i-propylamino, represents propenyloxy, representsdimethylamino or represents cyclopropyl,

[0090] R⁵ represents chlorine or bromine, represents in each caseoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in eachcase optionally fluorine-, chlorine- or bromine-substituted ethenyl,propenyl, butenyl, propinyl or butinyl, represents in each caseoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substitutedmethoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representspropenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio,propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino,butenylamino, propinylamino or butinylamino, represents dimethylamino,diethylamino or dipropylamino, represents in each case optionallyfluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy,cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio,cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio,cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino orcyclohexylmethylamino, or represents in each case optionally fluorine-,chlorine-, methyl-, trifluoromethyl-, methoxy- and/ormethoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy,phenylthio, benzylthio, phenylamino or benzylamino, or

[0091] R⁴ and R⁵ together represent optionally branched alkanediylhaving 3 to II carbon atoms.

[0092] The abovementioned general or preferred radical definitions applyboth to the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with each otheras desired, that is to say combinations between the stated preferredranges are also possible.

[0093] Using, for example, 4-bromo-2-methyl-thiophene-3-sulphonamide and5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-thioneas starting materials, the course of the reaction in the process (a)according to the invention can be illustrated by the following equation:

[0094] Using, for example, 4-chloro-2-ethyl-3-thienylsulphonylisothiocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of the reaction in the process (b)according to the invention can be illustrated by the following equation:

[0095] Using, for example, 4-ethyl-2-methoxy-thiophene-3-sulphonylchloride, 5-ethylthio-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one andpotassium cyanate as starting materials, the course of the reaction inthe process (c) according to the invention can be illustrated by thefollowing equation:

[0096] Using, for example, 4-cyano-2-isopropyl-thiophene-3-sulphonylchloride and 5-methyl-1,2,4-oxadiazole-3-carboxamide as startingmaterials, the course of the reaction in the process (d) according tothe invention can be illustrated by the following equation:

[0097] Using, for example,N-(4-fluoro-2-trifluoromethyl-thiophen-3-yl-sulphonyl)-O-methyl-urethaneand 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one as startingmaterials, the course of the reaction in the process (e) according tothe invention can be illustrated by the following equation:

[0098] The formula (II) provides a general definition of thesulphonamides to be used as starting materials in the process (a)according to the invention for preparing the compounds of the formula(I). In the formula (II), R¹ and R² each preferably or in particularhave those meanings which have already been mentioned above, in thedescription of the compounds of the formula (I) according to theinvention, as being preferred or as being particularly preferred for R¹and R².

[0099] The starting materials of the formula (II) have hitherto not beendisclosed in the literature; as novel substances, they also form part ofthe subject-matter of the present application.

[0100] The novel sulphonamides of the formula (II) are obtained whensulphonyl chlorides of the formula (VI)

[0101] in which

[0102] R¹ and R² are each as defined above,

[0103] are reacted with ammonia, if appropriate in the presence of adiluent, such as, for example, water, at temperatures between 0° C. and50° C. (cf. the Preparation Examples).

[0104] The sulphonyl chlorides of the formula (VI) have likewisehitherto not been disclosed in the literature; as novel substances, theyalso form part of the subject-matter of the present application.

[0105] The novel sulphonyl chlorides of the formula (VI) are obtainedwhen corresponding amino compounds of the general formula (X)

[0106] in which

[0107] R¹ and R² are each as defined above,

[0108] are reacted with an alkali metal nitrite, such as, for example,sodium nitrite, in the presence of hydrochloric acid at temperaturesbetween −10° C. and +10° C. and the resulting diazonium salt solution isreacted with sulphur dioxide in the presence of a diluent, such as, forexample, dichloromethane, 1,2-dichloroethane or acetic acid, and in thepresence of a catalyst, such as, for example, copper(I) chloride and/orcopper(II) chloride, at temperatures between −10° C. and +50° C. (cf.the Preparation Examples).

[0109] The amino compounds of the formula (X) required as precursors areknown and/or can be prepared by processes known per se (cf. DE 33 03388).

[0110] The formula (III) provides a general definition of the(thio)carboxylic acid derivatives further to be used as startingmaterials in the process (a) according to the invention for preparingthe compounds of the formula (I). In the formula (III), Q and R³ eachpreferably or in particular have that meaning which has already beenmentioned above, in the description of the compounds of the formula (I)according to the invention, as being preferred or as being particularlypreferred for Q and R³; Z preferably represents fluorine, chlorine,bromine, C₁-C₄-alkoxy, phenoxy or benzyloxy, in particular representschlorine, methoxy, ethoxy or phenoxy.

[0111] The starting materials of the formula (III) are known and/or canbe prepared by processes known per se (cf. EP 459244, EP 341489, EP422469, EP 425948, EP 431291, EP 507171, EP 534266).

[0112] The formula (IV) provides a general definition of the sulphonyliso(thio)cyanates to be used as starting materials in the process (b)according to the invention for preparing the compounds of the formula(I). In the formula (IV), Q, R¹ and R² each preferably or in particularhave that meaning which has already been mentioned above, in thedescription of the compounds of the formula (I) according to theinvention, as being preferred or as being particularly preferred for Q,R¹ and R².

[0113] The sulphonyl iso(thio)cyanates of the formula (IV) have hithertonot been disclosed in the literature; as novel substances, they alsoform part of the subject-matter of the present application.

[0114] The novel sulphonyl iso(thio)cyanates of the formula (IV) areobtained when sulphonamides of the general formula (II)—above—arereacted with phosgene and thiophosgene, respectively, if appropriate inthe presence of an alkyl isocyanate, such as, for example, butylisocyanate, if appropriate in the presence of a reaction auxiliary, suchas, for example, diazabicyclo[2.2.2]octane, and in the presence of adiluent, such as, for example, toluene, xylene or chlorobenzene, attemperatures between 80° C. and 150° C. and the volatile components aredistilled off under reduced pressure after the reaction has ended (cf.the Preparation Examples).

[0115] The formula (V) provides a general definition of the heterocyclesto be used as starting materials in the processes (b), (c) and (e)according to the invention. In the formula (V), R³⁻¹ preferablyrepresents optionally substituted triazolinyl of the formula below

[0116] in which Q¹ represents oxygen or sulphur and the radicals R⁴ andR⁵ each preferably or in particular have those meanings which havealready been mentioned above, in the description of the compounds of theformula (I) according to the invention, as being preferred or as beingparticularly preferred for R⁴ and R⁵.

[0117] The starting materials of the formula (V) are known and/or can beprepared by processes known per se (cf. EP 341489, EP 422469, EP 425948,EP 431291, EP 507171, EP 534266).

[0118] The formula (VI) provides a general definition of the sulphonylchlorides to be used as starting materials in the processes (c) and (d)according to the invention for preparing the compounds of the formula(I). In the formula (VI), R¹ and R² each preferably or in particularhave that meaning which has already been mentioned above, in thedescription of the compounds of the formula (1) according to theinvention, as being preferred or as being particularly preferred for R¹and R².

[0119] The sulphonyl chlorides of the formula (VI) have hitherto notbeen disclosed in the literature; as novel substances, they also formpart of the subject-matter of the present application and they can beprepared as described above.

[0120] The formula (VIII) provides a general definition of the(thio)carboxamides to be used as starting materials in the process (d)according to the invention for preparing the compounds of the formula(I). In the formula (VIII), Q and R³ each preferably or in particularhave that meaning which has already been mentioned above, in thedescription of the compounds of the formula (I) according to theinvention, as being preferred or as being particularly preferred for Qand R³.

[0121] The starting materials of the formula (VIII) are known and/or canbe prepared by processes known per se (cf. EP 459244).

[0122] The formula (IX) provides a general definition of thesulphonylamino(thio)carbonyl compounds to be used as starting materialsin the process (e) according to the invention for preparing thecompounds of the formula (I). In the formula (IX), Q, R¹ and R² eachpreferably or in particular has that meaning which has already beenmentioned above, in the description of the compounds of the formula (I)according to the invention, as being preferred or as being particularlypreferred for Q, R¹ and R²; Z preferably represents fluorine, chlorine,bromine, C₁-C₄-alkoxy, phenoxy or benzyloxy, in particular representschlorine, methoxy, ethoxy or phenoxy.

[0123] The starting materials of the formula (IX) are known and/or canbe prepared by processes known per se.

[0124] The processes (a), (b), (c), (d) and (e) according to theinvention for preparing the novel compounds of the formula (I) arepreferably carried out using diluents Suitable diluents are virtuallyall inert organic solvents. These preferably include aliphatic andaromatic, optionally halogenated hydrocarbons such as pentane, hexane,heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene,toluene, xylene, methylene chloride, ethylene chloride, chloroform,carbon tetrachloride, chlorobenzene and o-dichlorobenzene; ethers suchas diethyl ether and dibutyl ether, glycol dimethyl ether and diglycoldimethyl ether, tetrahydrofuran and dioxane; ketones such as acetone,methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone;esters such as methyl acetate and ethyl acetate; nitrites such as, forexample, acetonitrile and propionitrile; amides such as, for example,dimethylformamide, dimethylacetamide and N-methylpyrrolidone and alsodimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphorictriamide.

[0125] Suitable reaction auxiliaries or acid acceptors for use in theprocesses (a), (b), (c), (d) and (e) according to the invention are allacid binders which can conventionally be used for such reactions.Preference is given to alkali metal hydroxides such as, for example,sodium hydroxide and potassium hydroxide, alkaline earth metalhydroxides such as, for example, calcium hydroxide, alkali metalcarbonates and alkoxides such as sodium carbonate and potassiumcarbonate, sodium tert-butoxide and potassium tert-butoxide, furthermorebasic nitrogen compounds, such as trimethylamine, triethylamine,tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine,ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethyl-benzylamine,N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4,3,0]-non-5-ene (DBN),1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) and1,4-diazabicyclo-[2,2,2]-octane (DABCO).

[0126] The reaction temperatures in the processes (a), (b), (c), (d) and(e) according to the invention can be varied within a relatively widerange. In general, the processes are carried out at temperatures between−20° C. and +150° C., preferably at temperatures between 0° C. and +100°C.

[0127] The processes (a), (b), (c), (d) and (e) according to theinvention are generally carried out under atmospheric pressure. However,it is also possible to operate under elevated or reduced pressure.

[0128] For carrying out the processes (a), (b), (c), (d) and (e)according to the invention, the starting materials which are required ineach case are generally employed in approximately equimolar amounts.However, it is also possible to employ a relatively large excess of oneof the components used in each case. The reactions are generally carriedout in a suitable diluent in the presence of an acid acceptor, and thereaction mixture is stirred for a number of hours at the respectivetemperature required. Work-up in the processes (a), (b), (c), (d) and(e) according to the invention is in each case carried out by customarymethods (cf. the Preparation Examples).

[0129] If required, salts can be prepared from the compounds of thegeneral formula (I) according to the invention. Such salts are obtainedin a simple manner by customary salt formation methods, for example bydissolving or dispersing a compound of the formula (I) in a suitablesolvent, such as, for example, methylene chloride, acetone, tert-butylmethyl ether or toluene, and adding a suitable base. The salts can thenbe isolated—if appropriate after prolonged stirring—by concentration orfiltration with suctio

[0130] The active compounds according

ed as defoliants, desiccants, haulm killers and, espec

ds in the broadest sense, there are to be understood all

ns where they are not wanted. Whether the substances according to theinvention act as total or selective herbicides depends essentially onthe amount used.

[0131] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0132] Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoca,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindemia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

[0133] Dicotyledonous crops of the genera: Gossypium, Glycine, Beta,Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

[0134] Monocotyledonous weeds of the genera: Echinochloa, Setaria,Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium,Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria,Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum,Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera

[0135] Monocotyledonous crops of the genera: Oryza, Zea, Triticum,Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagusand Allium.

[0136] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0137] The compounds are suitable, depending on the concentration, forthe total control of weeds, for example on industrial terrain andrailway tracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for the control of weeds inperennial crops for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and for the selective control of weeds inannual cultures.

[0138] The compounds of the formula (I) according to the invention aresuitable in particular for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous crops, both pre-emergence andpost-emergence.

[0139] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusting agents, pastes, soluble powders, granules,suspo-emulsion concentrates, natural and synthetic materials impregnatedwith active compound, and very fine capsules in polymeric substances.

[0140] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is liquid solventsand/or solid carriers, optionally with the use of surface-active agents,that is emulsifying agents and/or dispersing agents and/or foam-formingagents.

[0141] If the extender used is water, it is also possible to employ forexample organic solvents as auxiliary solvents. Suitable liquid solventsare essentially the following: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and also water.

[0142] Suitable solid carriers are: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,and also synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifying and/or foam-forming agents are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates aswell as protein hydrolysates; suitable dispersing agents are: forexample lignin-sulphite waste liquors and methylcellulose.

[0143] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latexes, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

[0144] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyes,such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

[0145] The formulations in general contain between 0.1 and 95 percent byweight of active compound, preferably between 0.5 and 90%.

[0146] For the control of weeds, the active compounds according to theinvention, as such or in the form of their formulations, can also beused as mixtures with known herbicides, finished formulations or tankmixes being possible.

[0147] Possible components for the mixtures are known herbicides, forexample acetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, asulam,atrazine, azimsulfuron, benazolin, benfuresate, bensulfuron(-methyl),bentazon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox,bromobutide, bromofenoxim, bromoxynil, butachlor, butylate, cafenstrole,carbetamide, chlomethoxyfen, chloramben, chloridazon,chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron,cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone,clopyralid, clopyrasulfuron, cloransulam(-methyl), cumyluron, cyanazine,cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB,2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), difenzoquat,diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dinitramine, diphenamid, diquat, dithiopyr, diuron,dymron, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl),ethofinnesate, ethoxyfen, etobenzanid, fenoxaprop(-ethyl),flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),flazasulfuron, fluazifop(-butyl), flumetsulam, flumiclorac(-pentyl),flumioxazin, flurnipropyn, fluometuron, fluorochloridone,fluoroglycofen(-ethyl), flupoxam, flupropacil, flurenol, fluridone,fluroxypyr, flurprimidol, flurtamone, fomesafen, glufosinate(-ammonium),glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl),hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapyr,imazaquin, imazethapyr, imazosulfuron, ioxynil, isopropalin,isoproturon, isoxaben, isoxaflutole, isoxapyrifop, lactofen, lenacil,linuron, MCPA, MCPP, mefenacet, metamitron, metazachlor,methabenzthiazuron, metobenzuron, metobromuron, metolachlor, metosulam,metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron,naproanilide, napropamide, neburon, nicosulfuron, norflurazon,orbencarb, oryzalin, oxadiazon, oxyfluorfen, paraquat, pendimethalin,phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl),prometryn, propachlor, propanil, propaquizafop, propyzamide,prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron(-ethyl),pyrazoxyfen, pyributicarb, pyridate, pyrithiobac(-sodium), quinchlorac,quinmerac, quizalofop(-ethyl), quizalofop(-p-teftiryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone,sulfometuron(-methyl), sulfosate, tebutam, tebuthiuron, terbuthylazine,terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin,thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim,triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane,trifluralin and triflusulfiron.

[0148] Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, are also possible.

[0149] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

[0150] The active compounds according to the invention can be appliedeither before or after emergence of the plants. They can also beincorporated into the soil before sowing.

[0151] The amount of active compound used can vary within a substantialrange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

[0152] The preparation and use of the active compounds according to theinvention can be seen from the examples below.

PREPARATION EXAMPLES Example 1

[0153]

[0154] (Process (a))

[0155] 1.3 g (6.8 mmol) of 2,4-dimethyl-thiophene-3-sulphonamide and 1.1g (7 mmol) of 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) are addedsuccessively to a solution of 1.6 g (6.4 mmol) of5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-onein 30 ml of acetonitrile. The reaction mixture is stirred at roomtemperature (about 20° C.) for approximately 15 hours and subsequentlyconcentrated under waterpump vacuum. The residue is then taken up inmethylene chloride and washed with 1N hydrochloric acid and then withwater. The organic phase is dried with magnesium sulphate and filtered.The filtrate is concentrated under waterpump vacuum and the residue isrecrystallized from isopropanol.

[0156] This gives 1.1 g (50% of theory) of5-ethoxy-4-methyl-2-(2,4-dimethyl-thien-3-yl-sulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 158° C.

Example 2

[0157]

[0158] (Process (d))

[0159] At 20° C. to at most 35° C., 2.0 g (36 mmol) of potassiumhydroxide powder are added to a solution of 1.52 g (12.0 mmol) of5-methyl-1,2,4-oxadiazol-3-carboxamide in 150 ml of dioxane. After 30minutes, approximately 50 ml of dioxane are distilled off at from 30° C.to 35° C. under waterpump vacuum. The mixture is subsequently admixed alittle at a time with 2.65 g (12.6 mmol) of2,4-dimethyl-thiophene-3-sulphonyl chloride and the reaction mixture isstirred at room temperature (about 20° C.) for approximately 12 hours.The mixture is subsequently concentrated under waterpump vacuum and theresidue is taken up in water and acidified with 2N hydrochloric acid.The mixture is then extracted twice with 100 ml of methylene chlorideeach time. The combined organic solutions are washed with water, driedwith magnesium sulphate and filtered. The filtrate is concentrated underwaterpump vacuum and the residue is recrystallized from ethanol.

[0160] This gives 0.7 g (19% of theory) ofN-(2,4-dimethyl-thien-3-yl-sulphonyl)-5-methyl-1,2,4-oxadiazol-3-carboxamideof melting point 164° C.

[0161] By the methods of Examples 1 and 2, and in accordance with thegeneral description of the preparation processes according to theinvention, it is also possible to prepare, for example, the compounds ofthe formula (I) listed in Table I below.

TABLE 1 Examples of compounds of the formula (I) Melt- ing Ex. point No.Q R¹ R² R³ (° C.) 3 O CH₃ CH₃

152 4 O CH₃ CH₃

179 5 O CH₃ CH₃

120 6 O CH₃ CH₃

137 7 O CH₃ CH₃

122 8 O CH₃ CH₃

107 9 O CH₃ CH₃

63 10 O CH₃ CH₃

130 11 O CH₃ CH₃

96 12 O CH₃ CH₃

82 13 O CH₃ CH₃

129 14 O CH₃ CH₃

117 15 O CH₃ CH₃

159 16 S CH₃ CH₃

124 17 O CH₃ CH₃

91 18 O CH₃ CH₃

128 19 O CH₃ CH₃

70 20 O CH₃ CH₃

55 21 O CH₃ CH₃

114 22 O CH₃ CH₃

163 23 O CH₃ CH₃

95 24 O CH₃ CH₃

129 25 O CH₃ CH₃

177 26 O CH₃ CH₃

165 27 O CH₃ CH₃

160 28 O CH₃ CH₃

62 29 O CH₃ CH₃

164 30 O CH₃ CH₃

125 31 O CH₃ CH₃

74 32 O CH₃ CH₃

158 33 S CH₃ CH₃

112 34 S CH₃ CH₃

147 35 S CH₃ CH₃

139 36 S CH₃ CH₃

136 37 S CH₃ CH₃

78 38 S CH₃ CH₃

97 39 O CH₃ CH₃

66 40 O CH₃ OCH₃

41 O CH₃ OCH₃

42 O CH₃ OCH₃

43 O CH₃ OCH₃

[0162] Starting Materials of the Formula (II):

Example (11-1)

[0163]

[0164] A mixture of 6.0 g (29 mmol) of2,4-dimethyl-thiophene-3-sulphonyl chloride and 30 ml of 25% strengthaqueous ammonia solution is stirred at room temperature (about 20° C.)for 12 hours. The resulting crystalline product is then isolated byfiltration with suction.

[0165] This gives 4.3 g (80% of theory) of2,4-dimethyl-thiophene-3-sulphonamide of melting point 135° C.

[0166] Starting Materials of the Formula (IV):

Example (IV-1)

[0167]

[0168] A mixture of 19.1 g (100 mmol) of2,4-dimethyl-thiophene-3-sulphonamide, 10.0 g (100 mmol) of butylisocyanate and 100 ml of chloroform is heated to the boil, and phosgeneis introduced into the mixture at reflux temperature for 4 hours. Themixture is subsequently concentrated under waterpump vacuum and theresidue is subjected to distillation under oilpump vacuum.

[0169] This gives 10.3 g (47% of theory) of2,4-dimethyl-thien-3-yl-sulphonyl isocyanate of a boiling range of from135° C. to 140° C. (at 1 mbar).

[0170] Starting Materials of the Formula (VI):

Example (VI-1)

[0171]

[0172] A solution of 13.9 g (109 mmol) of 3-amino-2,4-dimethyl-thiophenein 30 ml of 10% strength hydrochloric acid is cooled to 0° C. andadmixed with 50 ml of conc. hydrochloric acid. With cooling to from 0°C. to −5° C., a solution of 8.6 g (125 mmol) of sodium nitrite in 22 mlof water is then added dropwise with stirring. The reaction mixture isstirred at from 0° C. to −5° C. for approximately one hour. Excesssodium nitrite is subsequently destroyed using amidosulphonic acid. Theresulting diazonium salt solution is added dropwise, at about 15° C., toa solution of 12 g of sulphur dioxide in 100 ml of 1,2-dichloro-ethane.600 mg of copper(I) chloride and 600 mg of dodecyl-trimethylammoniumbromide are then added and the reaction mixture is stirred at about 40°C. for approximately one hour and at room temperature (about 20° C.) fora further 12 hours. After addition of 6 g of 30% strength hydrogenperoxide solution, the mixture is stirred for a further 30 minutes. Theorganic phase is then separated off, washed twice with water, dried withmagnesium sulphate and filtered. The filtrate is concentrated underwaterpump vacuum, the residue is digested with petroleum ether and theresulting crystalline product is isolated by filtration with suction.

[0173] This gives 9.6 g (42% of theory) of2,4-dimethyl-thiophene-3-sulphonyl chloride of melting point 79° C.

[0174] In each case by the methods of Examples (II-1), (IV-1) and (VI-1)it is also possible to prepare, for example, the compounds of theformulae (II), (IV) and (VI) listed in Table 2 below:

TABLE 2 Examples of the compounds of the formulae (II), (IV) and (VI)[i.e. the radicals R¹ and R² apply to each of these 3 formulae]; Q is Oor S. Example No. II- IV- VI- R¹ R² 2 CH₃ C₂H₅ 3 CH₃ C₃H₇-n 4 CH₃ C₃H₇-i5 CH₃ CF₃ 6 CH₃ Cl 7 CH₃ OCH₃ 8 CH₃ OC₂H₅ 9 CH₃ OC₃H₇-n 10 CH₃ OC₃H7-i11 C₂H₅ CH₃ 12 C₃H₇-n CH₃ 13 C₃H₇-i CH₃

USE EXAMPLES Example A

[0175] Pre-Emergence Test

[0176] Solvent: 5 parts by weight of acetone

[0177] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0178] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0179] Seeds of the test plants are sown in normal soil. After about 24hours, the soil is watered with the preparation of the active compound.Advantageously, the amount of water per unit area is kept constant. Theactive compound concentration in the preparation is not important, onlythe active compound application rate per unit area is critical.

[0180] After three weeks, the degree of damage to the plants is rated in% damage in comparison with the development of the untreated control.The figures denote:

[0181] 0%=no effect (like untreated control)

[0182] 100%=total destruction

[0183] In this test, for example, the compounds of Preparation Example1, 3, 4, 5, 11 and 12 exhibit very strong activity against weeds, andsome of them are tolerated well by crop plants, such as, for example,maize and wheat (cf. Table A).

[0184] “ai.” (active ingredient)=active compound TABLE A Pre-emergencetest/greenhouse Applica- Active compound of tion rate PreparationExample (g of Chenopo- Sola- No. ai./ha) Maize Bromus Cyperus LoliumSetaria dium Matricaria num

125 5 100 100 100 100 100 100 100 (3) Applica- Active compound of tionrate Preparation Example (g of Chenopo- Sola- No. ai./ha) Wheat BromusCyperus Lolium Setaria dium Matricaria num

125 0 100 95 100 100 100 100 100 (1) Applica- Active compound of tionrate Preparation Example (g of Bro- Lo- Se- Chenopo- Matri- Sola- No.ai./ha) Wheat Maize mus Cyperus lium taria dium caria num

125 0 0 95 95 100 100 90 90 80 (4) Applica- Active compound of tion ratePreparation Example (g of No. ai./ha) Bromus Cyperus Lolium SetariaChenopodium Matricaria Solanum

125 100 100 100 100 95 100 95 (11) Active compound of PreparationApplication rate Example No. (g of ai./ha) Alopecurus AbutilonAmaranthus Sinapis Xanthium

250 70 90 90 95 90 (5)

250 70 90 90 95 — (12)

Example B

[0185] Post-Emergence Test

[0186] Solvent: 5 parts by weight of acetone

[0187] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0188] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0189] Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is chosen so that the amounts ofactive compound desired in each case are applied in 1000 l of water/ha.

[0190] After three weeks, the degree of damage to the plants is rated in% damage in comparison with the development of the untreated control.

[0191] The figures denote:

[0192] 0%=no effect (like untreated control)

[0193] 100%=total destruction

[0194] In this test, for example, the compounds of Preparation Examples6, 13 and 14 exhibit very strong activity against weeds, and some ofthem are tolerated well by crop plants, such as, for example, maize (cf.Table B). TABLE B Post-emergence test/greenhouse Active compoundApplica- of Preparation tion rate Amaran- Example No. (g of ai/ha) MaizeSetaria Abutilon thus Sinapis

250 10 80 —  90 100 (6)

250 — 80 80 100 100 (13)

250 10 90 —  95  95 (14)

1. Thienylsulphonylamino(thio)carbonyl compounds of the general formula

in which Q represents oxygen or sulphur, R¹ represents cyano, halogen orin each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substitutedalkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinytoxy having in eachcase up to 6 carbon atoms, R² represents cyano, halogen or in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkenyl,alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6carbon atoms, and R³ represents in each case optionally substitutedheterocyclyl having 5 ring members, at least one of which representsoxygen, sulphur or nitrogen and one to three others may representnitrogen, and salts of compounds of the formula (1).
 2. Compounds of theformula (I) according to claim 1, characterized in that Q representsoxygen or sulphur, R¹ represents cyano, halogen, represents optionallycyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents ineach case optionally cyano- or halogen-substituted C₂-C₄-alkenyl orC₂-C₄-alkinyl, represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each caseoptionally cyano- or halogen-substituted C₂-C₄-alkenyloxy orC₂-C₄-alkinyloxy, R² represents cyano, halogen, represents optionallycyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents ineach case optionally cyano- or halogen-substituted C₂-C₄-alkenyl orC₂-C₄-alkinyl, represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each caseoptionally cyano- or halogen-substituted C₂-C₄-alkenyloxy orC₂-C₄-alkinyloxy, and R³ represents in each case optionally substitutedheterocyclyl of the formulae below

 in which Q¹, Q² and Q³ each represent oxygen or sulphur and R⁴represents hydrogen, hydroxyl, amino, cyano, representsC₂-C₁₀-alkylideneamino, represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, represents in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₂-C₆-alkenylor C₂-C₆-alkinyl, represents in each case optionally fluorine-,chlorine-, bromine-, cyano-, C₁-C₄-alkoxy- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino orC₁-C₆-alkyl-carbonylamino, represents C₃-C₆-alkenyloxy, representsdi-(C₁-C₄-alkyl)-amino, represents in each case optionally fluorine-,chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkylamino or C₃-C₆-cycloalkyl-C₁-C₄-alkyl,or represents in each case optionally fluorine-, chlorine-, bromine-,cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl and/orC₁-C₄-alkoxy-substituted phenyl or phenyl-C₁-C₄-alkyl, R⁵ representshydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine,iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-,C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, represents in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₂-C₆-alkenylor C₂-C₆-alkinyl, represents in each case optionally fluorine-,chlorine-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substitutedC₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino orC₁-C₆-alkyl-carbonylamino, represents C₃-C₆-alkenyloxy,C₃-C₆-alkinyloxy, C₃-C₆-alkenylthio, C₃-C₆-alkinylthio,C₃-C₆-alkenylamino or C₃-C₆-alkinylamino, representsdi-(C₁-C₄-alkyl)-amino, represents in each case optionally methyl-and/or ethyl-substituted aziridino, pyrrolidino, piperidino ormorpholino, represents in each case optionally fluorine-, chlorine-,bromine-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio,C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkylthio orC₃-C₆-cycloalkyl-C₁-C₄-alkylamino, or represents in each case optionallyfluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substitutedphenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio,phenyl-C₁-C₄-alkylthio, phenylamino or phenyl-C₁-C₄-alkylamino, or R⁴and R⁵ together represent optionally branched alkanediyl having 3 to 11carbon atoms, furthermore R⁶, R⁷ and R⁸ are identical or different andeach represent hydrogen, cyano, fluorine, chlorine, bromine, orrepresent in each case optionally fluorine-, chlorine-, bromine- orC₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy,alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulphinyl oralkylsulphonyl having in each case up to 6 carbon atoms or representoptionally cyano-, fluorine-, chlorine-, bromine orC₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, and thesodium, potassium, magnesium, calcium, ammonium, C₁-C₄-alkylammonium,di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium,tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- orC₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts ofcompounds of the formula (I).
 3. Process for preparingthienylsulphonylamino(thio)carbonyl compounds of the general formula (I)according to claim 1 characterized in that (a) sulphonamides of thegeneral formula (II),

 in which R¹ and R² are each as defined in claim 1,  are reacted with(thio)carboxylic acid derivatives of the general formula (III),

 in which Q and R³ are each as defined in claim 1 and Z representshalogen, alkoxy, aryloxy or arylalkoxy,  if appropriate in the presenceof an acid acceptor and if appropriate in the presence of a diluent, orin that (b) sulphonyl iso(thio)cyanates of the general formula (IV)

 in which Q, R¹ and R² are each as defined above,  are reacted withheterocycles of the general formula (V) H—R³⁻¹  (V)  in which R³⁻¹represents optionally substituted heterocyclyl having 5 ring members, atleast one of which represents >N—H,  if appropriate in the presence of areaction auxiliary and if appropriate in the presence of a diluent, orin that (c) sulphonyl chlorides of the general formula (VI)

 in which R¹ and R² are each as defined above,  are reacted withheterocycles of the general formula (V) H—R³⁻¹  (V)  in which R³⁻¹ is asdefined above under (b),  and metal (thio)cyanates of the generalformula (VII) MQCN  (VII)  in which Q is as defined above and Mrepresents a metal equivalent,  if appropriate in the presence of areaction auxiliary and if appropriate in the presence of a diluent, orin that (d) sulphonyl chlorides of the general formula (VI)

 in which H—R³⁻¹  (V)  in which R³⁻¹ is as defined above under (b),  ifappropriate in the presence of an acid acceptor and if appropriate inthe presence of a diluent, and the compounds of the formula (I) obtainedby the processes (a), (b), (c), (d) or (e) are, if appropriate,converted into salts by customary methods.
 4. Herbicidal compositions,characterized in that they contain at least one compound of the formula(1) or a salt thereof according to claim
 1. 5. The use of compounds ofthe general formula (I) or salts thereof according to claim 1 forcontrolling undesirable vegetation.
 6. Method for controlling weeds,characterized in that compounds of the general formula (1) or saltsthereof according to claim 1 are allowed to act on the weeds or theirhabitat.
 7. Process for preparing herbicidal compositions, characterizedin that compounds of the general formula (I) or salts thereof accordingto claim 1 are mixed with extenders and/or surfactants.
 8. Sulphonamidesof the general formula (II),

R¹ and R² are each as defined above, are reacted with (thio)carboxamidesof the general formula (VIII)

 in which Q and R³ are each as defined above under formula (I) in claim1,  if appropriate in the presence of an acid acceptor and ifappropriate in the presence of a diluent, or in that (e)sulphonylamino(thio)carbonyl compounds of the general formula (IX)

 in which Q, R¹ and R² are each as defined above and Z representshalogen, alkoxy, aryloxy or arylalkoxy, are reacted with heterocycles ofthe general formula (V)  in which R¹ and R² are each as defined inclaim
 1. 9. Sulphonyl iso(thio)cyanates of the general formula (IV),

in which Q, R¹ and R² are each as defined in claim
 1. 10. SulphonylChlorides of the general formula (VI),

in which R¹ and R² are each as defined in claim 1.